San Diego Santa Run 5K
San Diego Santa Run 5K | San Diego Running Co.
San Diego Santa Run 5K | San Diego Running Co.
Events

The Most Festive Things to Do in San Diego This Holiday Season

Including a Santa-themed pub crawl, and also non-Santa things.

It's easy to lose track of the seasons if you're in San Diego, smugly strolling around in shorts and sandals while the rest of the nation freezes over. There's no mistaking the arrival of the holidays, though, and while the nonstop festive vibes can get a bit cloying after a while, there are plenty of holiday events worth braving the tinsel and carols for. In fact, there are so many festivals and parties around town that it can be hard to decide which ones to go to. Well, stop fretting: here are all the holiday happenings you need to mark on your calendar, all together in one... well, calendar.

Skate for a cause

November 14, 2019 - January 5, 2020
Liberty Station
Lace up your skates and hit the ice at Rady Children’s Ice Rink in the Arts District at Liberty Station. With 100% of the net proceeds going to benefit The Peckham Center for Cancer and Blood Disorders at Rady Children’s Hospital, the annual event has raised more than $1 million dollars over the past 19 years. Skate to your heart’s content, then visit one of Liberty Station’s restaurants and breweries, or stop by the Liberty Public Market for even more food and drink choices. 
Cost:  $10-15, includes skates and helmet rental

Embrace your inner Scrooge

November 21 -  December 22
Diversionary Theatre
The Santaland Diaries takes a cynical, sarcastic look at the self-imposed holiday stresses we endure in David Sedaris’ uproarious retelling of his stint as one of Santa’s elves Macy’s New York City Santaland. From inebriated Santas to tantruming toddlers, you’ll love this one-man narrative that’s by turns sardonic and sweet. 
Cost: $15-40 

Enjoy a new twist on an old classic

November 23 - December 29
Old Globe Theatre
Speaking of Scrooge, we’re all familiar with Charles Dickens’ holiday story, A Christmas Carol, but Ebenezer Scrooge’s BIG San Diego Christmas Show at the Old Globe Theatre reimagines it as a comedy set in (of all places) San Diego. Quick-witted and extravagantly theatrical, it’s a family-friendly retelling full of music, laughter and a heartwarming lesson about the spirit of giving.
Cost: $30-99 +fees

Watch Santa come to town, San Diego-style

November 30
Seaport Village
Santa Claus ditches the red suit and sleigh to arrive in San Diego via surfboard. Head down to Seaport Village to see the jolly man himself hit town at 1pm near the Pier Café, with a little help from San Diego’s Dragon Boat crew, followed by a meet and greet and photo ops for the kids. Later, he’ll hop into a shiny red convertible for a festive parade down the boardwalk featuring live music, stilt walkers, and holiday cheer. Take advantage of Small Business Saturday and peruse Seaport Village’s 50+ diverse shops to stock up on holiday gifts before enjoying refreshments at one of its many pubs and eateries. 
Cost:  Free

Run around Pacific Beach in a Santa suit

December 14
Pacific Beach
Burn off some of those holiday calories and have a blast while you’re doing it at the San Diego Santa Run 5K and 1 Mile Race! Runners have several race options: a 5K, a Speedy Santa competitive mile, a kid’s mile, and a Santa’s helper mile for you and your dog. 5K participants receive a free Sunny Santa suit to wear that includes a short sleeved jacket, shorts, hat, belt, beard and, of course, sunglasses, plus a drink ticket (21+ only) good at local bars including Maverick's, 710 Beach Club, and Bub's. Proceeds from the race benefit the Pacific Beach Holiday Parade, which conveniently starts right after the races end. 
Cost: Depending on the run, registration costs $20-40

Chow down on chili and beer

December 1
North Park
The 10th Annual SoNo Fest & Chili Cook-Off features 40 local restaurants throwing down their best bowls of hot, hearty chili. Get a five taste ticket for $17, or throw in an extra $5 for a beautiful keepsake bowl handmade by the San Diego Ceramic Connection. Wash it down with libations from 24 brewers, cider makers, and vintners in a block-long beverage garden before heading to the two stages presenting local bands, a kids' fest with carnival games and bounce houses, 40 local artisan vendors, and a food truck court. All proceeds benefit McKinley Elementary School. 
Cost: $17 for 5 tastings, $22 includes a keepsake bowl

See Balboa Park get all Christmas-ified

December 6 - December 7
Balboa Park
San Diego’s iconic crown jewel is transformed into a winter wonderland with thousands of dazzling holiday lights, thanks to December Nights. This free, family-friendly event includes complimentary admission to Balboa Park museums from 5-9 pm, plus live music, dance performances, museum shopping and food from all over the world. Highlights include the International Christmas Festival at the House of Pacific Relations Cottages, a performance by the San Diego Gay Men’s Chorus, and a tree lighting ceremony with Mayor Kevin L. Faulconer at 6:05pm on Friday, as well as a wide variety of exhibitions and entertainment in the museums.
Cost: Free

Pub crawl with Santa and Mrs. Claus

December 7
Gaslamp Quarter
Deck yourself out in your best Santa outfit and prepare for more holiday cheer than you can handle. The evening begins with a complimentary welcome shot and 50% off drinks, then continues to share holiday joy at four different bars featuring complimentary cover charges, VIP entry with re-entry privileges, and great drink specials. Whether you’ve been naughty or nice, you’ll still receive a Santa hat at check-in.
Cost: $26.99-36.99 +fees, but tickets must be purchased in advance

Hop aboard the ugly sweater express

December 14
Balboa Park
Beer lovers can celebrate National Ugly Christmas Sweater Day (of course it exists) as The San Diego Model Railroad Museum hosts its 5th annual Ales n’ Rails Ugly Christmas Sweater Party. Enjoy unlimited tastings from local craft breweries including Mike Hess Brewing, Pizza Port Brewing Company, Societe Brewing Company and Boochcraft, with proceeds helping to fund the museum’s unique exhibits, public programs, and the overall operations.
Cost: $30 +fees for presale tickets, or $35 +fees at the door

Take part in a holiday pet parade

December 15
Gaslamp Quarter
Halloween isn’t the only holiday for costumes -- yes, you can let your furry, feathered, or scaled friend show off its finery at the 12th Annual Gaslamp Holiday Pet Parade. The parade starts under the Gaslamp Quarter Archway, and features prizes for the best pet, human, and group costumes in nine categories, as well as a pet expo and pet talent show. There’s also free live music, and entrants can grab a complimentary goodie bag filled with pet-related product samples and gifts. Best parade viewing is along 4th & 5th Avenues between E and K Street.
Cost: Free for spectators,  $15 per pet in advance, and $20 day-of

Have a Big Night NYE

December 31
Hilton Bayfront
Ten different party zones, unlimited drinks at twelve bars, a first class full buffet, and the hottest party bands and DJs make Big Night San Diego the biggest, most indulgent way to ring in the New Year. Wander through the Sapphire Stage & Ballroom, Retro DJ Ballroom (Best of '80s through dance tunes), Club Dance Ballroom, Indigo Club Room, Urban Dance Zone, and dining areas all in the major rooms. In the VIP area there are additional zones, VIP Lounges, VIP Club Zone and Velvet Rope Area. 
Cost: $89.99-$2500 +fees

Make with the yuks at an improv comedy show

December 31
Hillcrest
Laugh your way into 2020 at the National Comedy Theatre’s New Year’s Eve Spectacular! The fun improv comedy show, similar to Drew Carey’s Whose Line Is It Anyway?, is based completely on audience suggestions. Also included is a buffet dinner before and after the show and a champagne toast at midnight, as well as an after-show party with the cast as you count down the seconds to the new year. Tickets must be purchased online and in advance, though, so no walk-ups. 21+ only.
Cost: $79

Toast to 2018 on the water

December 31
Grape Street Pier
Stroll aboard a $25 million dollar yacht and party like a celebrity as you gaze at spectacular 360 degree views of the San Diego skyline. Dance at your own chosen pace with three levels of music. A huge variety of gourmet appetizers and an open bar all night long keeps the party going -- upgrade to VIP status for early boarding and an extra hour of drinking and mingling on the upper deck. Just bring your 21+ ID, and let the the voyage begin!
Cost: $154

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Mary Beth Abate is a San Diego-based freelance writer by way of Chicago and Los Angeles. Her hobbies include yoga, pickling and fermenting various vegetables and beverages, reading cookbooks and traveling around Mexico. Keep up with her experiments @MaryBeth_Abate.